Synthesis and Anticalcium Activity of New Compounds Containing the 2,3-Dihydro-1,4-dioxino[2,3-b]pyridine System

Sánchez, I. H.; Pujol, Maria Dolors; Guillaumet, Gérald; Massingham, R.; Monteil, Alexandre R.; Dureng, G; Winslow, E.

doi:10.3797/scipharm.aut-00-14

Cited by 7 publications

(4 citation statements)

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“…Intramolecular base-promoted cyclization of 24, using NaH in refluxing 1,2-dimethoxyethane (DME) furnished compound 25 which already possesses the desired bicyclic nucleus. Finally, O-debenzylation of 25 using FeCl 3 led to the corresponding 3-hydroxymethyl-1-methyl-2,3-dihydro-1H- [1,4]oxazin [2,3-b]pyridine system 26 in good yield (Scheme 4). Confirmation of the structure of 26 was obtained by analysis of its NMR data.…”

Section: Methodsmentioning

confidence: 97%

“…This step involved sequential conversion of the hydroxy group of 19 into the corresponding thiol intermediate that was not detected in the reaction media, followed by in situ intramolecular cyclization of 20, furnishing system 21. 19 The last step of the synthesis was the debenzylation of 21, using FeCl 3 20 affording the corresponding 3-hydroxymethyl-2,3-dihydro [1,4]-oxathiino[2,3-b]pyridine 22 (Scheme 3). 21 The structure of this compound was confirmed by its 1 H NMR spectrum and analytical data.…”

Section: Methodsmentioning

confidence: 99%

“…18 The 2,3-dihydro- [1,4]oxathiino [2,3-b]pyridine bicyclic core of 21 was prepared in one step from 19 by reaction with Lawesson's reagent in refluxing toluene. This step involved sequential conversion of the hydroxy group of 19 into the corresponding thiol intermediate that was not detected in the reaction media, followed by in situ intramolecular cyclization of 20, furnishing system 21.…”

Section: Methodsmentioning

confidence: 99%

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Novel analogues of 3-substituted-2,3-dihydro-1,4-dioxino[2,3-b]pyridines: modifications in the dioxane ring

Bartolomea¹,

Alcázar²,

Andrés³

et al. 2003

Tetrahedron Letters

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Section: Methodsmentioning

confidence: 97%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Novel analogues of 3-substituted-2,3-dihydro-1,4-dioxino[2,3-b]pyridines: modifications in the dioxane ring

Bartolomea¹,

Alcázar²,

Andrés³

et al. 2003

Tetrahedron Letters

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“…Bioisosteric replacement of benzene by pyridine in compounds containing the 2-substituted-2,3-dihydro-1,4-benzodioxin core [63] has yielded derivatives of biological interest in diverse therapeutic areas such as CNS (5-HT 1A receptor agonists 77 [64] and 78 [65]) and cardiovascular diseases (calcium antagonist 79 [66]) [ Fig. (4)].…”

Section: 4-benzodioxino[23-b]pyridinesmentioning

confidence: 99%

Syntheses of 2,3-Dihydro-1,4-Benzodioxins and Bioisosteres as Structural Motifs for Biologically Active Compounds

Cruz‐López¹,

Núñez²,

Conejo‐García³

et al. 2011

COC

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The 2,3-dihydro-1,4-benzodioxin ring system is present in a large number of structures of therapeutic agents possessing important biological activities. Some of them are antihypertensive agents. Others are involved in nervous breakdown and schizophrenia or represent an attractive therapeutic target for the treatment of glaucoma. The 2,3-dihydro-1,4-benzodioxin core has also been developed for the synthesis of inhibitors of 5-lipoxygenase and accordingly, these 2,3-dihydro-1,4-benzodioxins are useful for the treatment of inflammatory diseases such as asthma and arthritis. The synthesis and reactivity of several bioisosteres of the non-aromatic ring will be discussed. The occurrence of the 2,3-dihydro-1,4-benzodioxin structure in various naturally abundant compounds is also known. The total synthesis of angustureine (a novel 1,2,3,4-tetrahydroquinoline alkaloid with a n-pentyl side chain at position 2) will be presented. The bioisosteric replacement of benzene by pyridine in compounds containing the 2-substituted-2,3-dihydro-1,4-benzodioxin core has yielded derivatives of biological interest in diverse therapeutic areas such as central nervous system and cardiovascular diseases. These promising results have prompted interest in the area of 1,4-dioxino-[2,3-b]pyridine analogues. Several modifications on both the aromatic and the non-aromatic rings will be reviewed, including several transformations of the new heterocycles, such as the Smiles rearrangement. Moreover, the enantiomers of 2-and 3-hydroxymethyl-2,3-dihydro-1,4-dioxino-[2,3-b]pyridines, important chiral building blocks for the preparation of several biologically active compounds, have been synthesized. We have made an attempt to take into account the largest possible number of original papers, including our research and others. Publications of the last eleven years are included in this review.

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ChemInform Abstract: Synthesis and Anticalcium Activity of New Compounds Containing the 2,3‐Dihydro‐1,4‐dioxino[2,3‐b]pyridine System.

Sánchez¹,

Pujol²,

Guillaumet³

et al. 2000

ChemInform

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Synthesis and Anticalcium Activity of New Compounds Containing the 2,3-Dihydro-1,4-dioxino[2,3-b]pyridine System

Abstract: Summary: New compounds (3 and 4) possesing the 2,3-dihydro-1,4-dioxino[2,3-b]pyridine group were synthesized and tested as calcium antagonist agents. Both of them showed moderate anticalcium activity.

Cited by 7 publications

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Novel analogues of 3-substituted-2,3-dihydro-1,4-dioxino[2,3-b]pyridines: modifications in the dioxane ring

Novel analogues of 3-substituted-2,3-dihydro-1,4-dioxino[2,3-b]pyridines: modifications in the dioxane ring

Syntheses of 2,3-Dihydro-1,4-Benzodioxins and Bioisosteres as Structural Motifs for Biologically Active Compounds

ChemInform Abstract: Synthesis and Anticalcium Activity of New Compounds Containing the 2,3‐Dihydro‐1,4‐dioxino[2,3‐b]pyridine System.

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